#------------------------------------------------------------------------------
#$Date: 2025-08-19 20:17:10 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301807 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/01/2240190.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2240190
loop_
_publ_author_name
'Balaji, J.'
'John Francis Xavier, J.'
'Prabu, S.'
'Srinivasan, P.'
_publ_section_title
;
 Crystal structure of
 (E)-N'-(4-chlorobenzylidene)-4-methylbenzenesulfonohydrazide:
 a hexagonal polymorph
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1250
_journal_page_last               o1251
_journal_paper_doi               10.1107/S1600536814023721
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C14 H13 Cl N2 O2 S'
_chemical_formula_moiety         'C14 H13 Cl N2 O2 S'
_chemical_formula_sum            'C14 H13 Cl N2 O2 S'
_chemical_formula_weight         308.77
_chemical_name_systematic
;
(E)-N'-(4-Chlorobenzylidene)-4-methylbenzenesulfonohydrazide
;
_space_group_IT_number           169
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 61'
_symmetry_space_group_name_H-M   'P 61'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   10.8907(3)
_cell_length_b                   10.8907(3)
_cell_length_c                   21.4542(7)
_cell_measurement_reflns_used    9375
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.75
_cell_measurement_theta_min      2.35
_cell_volume                     2203.71(11)
_computing_cell_refinement
;
APEX2 and SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT and XPREP (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SIR92 (Altomare et al.,  1993)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22095
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.404
_exptl_absorpt_correction_T_max  0.9099
_exptl_absorpt_correction_T_min  0.8706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.162
_refine_ls_abs_structure_details
;
Flack (1983), 1257 Friedel pairs
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_coef       0.0026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL97 (Sheldrick, 2008)
;
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2586
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0306P)²+0.7106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0672
_refine_ls_wR_factor_ref         0.0718
_reflns_number_gt                2345
_reflns_number_total             2586
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2800sup1.cif
_cod_data_source_block           I
_cod_database_code               2240190
_cod_database_fobs_code          2240190
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, x, z+1/6'
'y, -x+y, z+5/6'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 -0.1026(3) -0.5080(4) 0.94696(15) 0.0727(9) Uani d . 1 1
H H1A -0.2001 -0.5364 0.9392 0.109 Uiso calc R 1 1
H H1B -0.0699 -0.4482 0.9831 0.109 Uiso calc R 1 1
H H1C -0.0942 -0.5906 0.9539 0.109 Uiso calc R 1 1
C C2 -0.0151(3) -0.4286(3) 0.89196(13) 0.0480(6) Uani d . 1 1
C C3 -0.0778(3) -0.4059(3) 0.84061(13) 0.0507(6) Uani d . 1 1
H H3 -0.1751 -0.4410 0.8405 0.061 Uiso calc R 1 1
C C4 0.0019(3) -0.3321(3) 0.78968(12) 0.0496(6) Uani d . 1 1
H H4 -0.0415 -0.3180 0.7553 0.060 Uiso calc R 1 1
C C5 0.1458(2) -0.2795(2) 0.79003(11) 0.0419(5) Uani d . 1 1
C C6 0.2103(3) -0.3013(3) 0.84070(12) 0.0483(6) Uani d . 1 1
H H6 0.3077 -0.2657 0.8408 0.058 Uiso calc R 1 1
C C7 0.1296(3) -0.3758(3) 0.89098(13) 0.0514(6) Uani d . 1 1
H H7 0.1730 -0.3911 0.9250 0.062 Uiso calc R 1 1
C C8 0.1633(3) 0.1027(3) 0.74279(11) 0.0426(5) Uani d . 1 1
H H8 0.2543 0.1797 0.7474 0.051 Uiso calc R 1 1
C C9 0.0430(3) 0.1244(3) 0.74794(10) 0.0415(5) Uani d . 1 1
C C10 -0.0947(3) 0.0146(3) 0.74508(13) 0.0520(6) Uani d . 1 1
H H10 -0.1127 -0.0766 0.7367 0.062 Uiso calc R 1 1
C C11 -0.2070(3) 0.0381(3) 0.75456(13) 0.0579(7) Uani d . 1 1
H H11 -0.3000 -0.0366 0.7526 0.069 Uiso calc R 1 1
C C12 -0.1789(3) 0.1731(3) 0.76682(12) 0.0522(6) Uani d . 1 1
C C13 -0.0439(3) 0.2844(3) 0.76863(13) 0.0574(7) Uani d . 1 1
H H13 -0.0266 0.3758 0.7763 0.069 Uiso calc R 1 1
C C14 0.0664(3) 0.2595(3) 0.75898(12) 0.0516(6) Uani d . 1 1
H H14 0.1589 0.3353 0.7599 0.062 Uiso calc R 1 1
O O1 0.3852(2) -0.1677(2) 0.73010(9) 0.0597(5) Uani d . 1 1
O O2 0.1652(2) -0.2455(2) 0.67125(8) 0.0605(5) Uani d . 1 1
S S1 0.24764(7) -0.18427(7) 0.72562(3) 0.04549(16) Uani d . 1 1
Cl Cl1 -0.31836(9) 0.20068(10) 0.78326(4) 0.0779(3) Uani d . 1 1
N N1 0.2735(2) -0.0230(2) 0.73014(10) 0.0445(5) Uani d D 1 1
N N2 0.1474(2) -0.0187(2) 0.73212(9) 0.0424(5) Uani d . 1 1
H H1 0.337(2) 0.033(2) 0.7573(10) 0.050(8) Uiso d D 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C7 C2 C3 118.4(2)
C7 C2 C1 121.2(3)
C3 C2 C1 120.3(2)
C4 C3 C2 120.9(2)
C4 C3 H3 119.5
C2 C3 H3 119.5
C5 C4 C3 119.6(2)
C5 C4 H4 120.2
C3 C4 H4 120.2
C4 C5 C6 120.4(2)
C4 C5 S1 119.71(18)
C6 C5 S1 119.89(19)
C7 C6 C5 119.4(2)
C7 C6 H6 120.3
C5 C6 H6 120.3
C6 C7 C2 121.2(2)
C6 C7 H7 119.4
C2 C7 H7 119.4
N2 C8 C9 121.5(2)
N2 C8 H8 119.3
C9 C8 H8 119.3
C10 C9 C14 118.3(2)
C10 C9 C8 122.5(2)
C14 C9 C8 119.1(2)
C9 C10 C11 120.9(2)
C9 C10 H10 119.6
C11 C10 H10 119.6
C12 C11 C10 118.8(3)
C12 C11 H11 120.6
C10 C11 H11 120.6
C13 C12 C11 121.6(2)
C13 C12 Cl1 119.5(2)
C11 C12 Cl1 118.8(2)
C12 C13 C14 118.8(2)
C12 C13 H13 120.6
C14 C13 H13 120.6
C13 C14 C9 121.5(3)
C13 C14 H14 119.3
C9 C14 H14 119.3
O2 S1 O1 119.65(12)
O2 S1 N1 106.40(11)
O1 S1 N1 104.78(11)
O2 S1 C5 107.80(12)
O1 S1 C5 109.72(11)
N1 S1 C5 107.91(11)
N2 N1 S1 113.13(16)
N2 N1 H1 113.4(17)
S1 N1 H1 116.2(17)
C8 N2 N1 114.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.491(4)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C7 1.381(3)
C2 C3 1.382(4)
C3 C4 1.376(4)
C3 H3 0.9300
C4 C5 1.374(3)
C4 H4 0.9300
C5 C6 1.378(3)
C5 S1 1.751(3)
C6 C7 1.372(4)
C6 H6 0.9300
C7 H7 0.9300
C8 N2 1.265(3)
C8 C9 1.447(3)
C8 H8 0.9300
C9 C10 1.374(3)
C9 C14 1.383(3)
C10 C11 1.384(4)
C10 H10 0.9300
C11 C12 1.369(4)
C11 H11 0.9300
C12 C13 1.360(4)
C12 Cl1 1.726(3)
C13 C14 1.373(4)
C13 H13 0.9300
C14 H14 0.9300
O1 S1 1.4197(18)
O2 S1 1.4189(19)
S1 N1 1.637(2)
N1 N2 1.399(3)
N1 H1 0.875(17)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O2 5_555 0.875(17) 2.133(19) 2.952(3) 156(2)
C1 H1A O1 5_445 0.96 2.55 3.496(5) 169
C13 H13 Cg 1_565 0.93 2.94 3.823(3) 160
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7 C2 C3 C4 -0.2(4)
C1 C2 C3 C4 179.7(3)
C2 C3 C4 C5 -0.4(4)
C3 C4 C5 C6 0.6(4)
C3 C4 C5 S1 -179.42(19)
C4 C5 C6 C7 -0.1(4)
S1 C5 C6 C7 179.9(2)
C5 C6 C7 C2 -0.5(4)
C3 C2 C7 C6 0.7(4)
C1 C2 C7 C6 -179.2(3)
N2 C8 C9 C10 3.7(4)
N2 C8 C9 C14 -179.3(2)
C14 C9 C10 C11 -1.6(4)
C8 C9 C10 C11 175.4(2)
C9 C10 C11 C12 0.1(4)
C10 C11 C12 C13 1.3(4)
C10 C11 C12 Cl1 -176.2(2)
C11 C12 C13 C14 -1.2(4)
Cl1 C12 C13 C14 176.3(2)
C12 C13 C14 C9 -0.4(4)
C10 C9 C14 C13 1.8(4)
C8 C9 C14 C13 -175.3(2)
C4 C5 S1 O2 -35.4(2)
C6 C5 S1 O2 144.6(2)
C4 C5 S1 O1 -167.3(2)
C6 C5 S1 O1 12.8(2)
C4 C5 S1 N1 79.1(2)
C6 C5 S1 N1 -100.9(2)
O2 S1 N1 N2 57.70(19)
O1 S1 N1 N2 -174.64(16)
C5 S1 N1 N2 -57.77(18)
C9 C8 N2 N1 -178.3(2)
S1 N1 N2 C8 172.28(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 6861424
